Woody Allen is a writer-director who I’ve always revered – his incredibly amount of output and passion for the arts is a great source of inspiration for me as a writer and film enthusiast. Even when his films are bad or mediocre, there’s passion and heart to them. His 1977 film Annie Hall is arguably the greatest film he’s ever made, featuring a great love story, hilarious Woody Allen dialogue, and terrific performances. Annie Hall stars Woody Allen as Alvy Singer, a neurotic comedian reflecting on his relationship with Annie Hall (Diane Keaton), which we find out has ended a year ago. Alvy chronicles his childhood in New York, where he obsessed over the meaning of his existence, and was punished for his early sexual curiosity. Through a series of flashbacks, Alvy and Annie meet after a doubles tennis game with friends, and the two awkwardly hit it off. Things progress wonderfully until Annie moves in with Alvy, which creates tension in the relationship. The two eventually break up, date other people, and reconcile shortly after when Annie needs Alvy’s help with killing a spider in the middle of the night. Soon after their reconciliation, the relationship once again falls apart, this time permanently – both characters are glad to have loved one another, even if it wasn’t always filled with good times. Annie Hall is one of the most beloved romantic comedies in Hollywood history – it even beat Star Wars for Best Picture at the 1978 Academy Awards. The screenplay by Woody Allen and Marshall Brickman is highly intelligent and often morbidly hilarious, playing on Woody Allen’s fascinations with death, existence, and the creative process. Even through the script’s intellectual and neurotic nature, Allen and Brickman manage to create one of the most genuine and heartfelt romantic stories ever told on film – one that doesn’t just focus on the best moments in a relationship. The use of flashbacks and non-linear storytelling allows for Allen and Brickman to explore the past of Alvy Singer, including the failed marriages and relationships that have shaped his views on romance. Both Woody Allen and Diane Keaton shine throughout Annie Hall, carrying dramatic and comedic weight like no other on-screen pairing could. Woody Allen’s Alvy Singer is his usual highly neurotic and obsessive, but still confident and arrogant, self, while Diane Keaton’s Annie Hall is adorably goofy, strong-willed, and highly intelligent. The two had such obvious on-screen chemistry in their many collaborations, undoubtedly aided by their brief real life romantic relationship. Annie Hall is Woody Allen at his absolute funniest as a writer and a performer, somehow managing to make both Ingmar Bergman and holocaust documentary The Sorrow and the Pity humorous. The writing and storytelling feels personal and genuine, and the film’s ending feels groundbreaking for the time – not giving the audience the “fairy tale”-esque ending they might be asking for. Annie Hall is Woody Allen’s greatest achievement as a writer and director, and may even be the film where he finally found his voice. It’s hilarious, romantic, heartbreaking, genuine, and smart – everything a Woody Allen movie should be.

Everybody reading through this list knows the basic story of Rocky – the ultimate underdog gets a chance to fight one of the most accomplished boxers in the world and takes him to the limit after weeks of hard work and training. The formula used by writer and star Sylvester Stallone in Rocky is an age old one, and yet feels so fresh in the Best Picture winning drama. Rocky tells the story of Rocky Balboa (Sylvester Stallone), a hard working Italian-American boxer living in Philadelphia. Rocky is in love with a painfully shy and timid pet store clerk named Adrian (Talia Shire), whose brother Paulie (Burt Young) is Rocky’s best friend. After finding out that his opponent for the big Bicentennial fight is out with an injury, world champion Apollo Creed (Carl Weathers) handpicks “The Italian Stallion” Rocky Balboa to be his opponent in five weeks. Rocky reluctantly accepts the fight, aided by Adrian, Paulie, and his trainer Mickey (Burgess Meredith), who pushes Rocky to the limit so that he might stand a chance against the much more experienced Creed. At this point in my life, I’ve seen Rocky dozens of times, and even after all these years, John G. Avildsen’s film makes me feel so energetic, inspired, and emotional. When the film’s iconic ending comes, I’m in tears no matter who I’m watching with – it’s just the kind of wholly satisfying endings you rarely gets in the movies. Rocky’s underdog story never feels cliche or false, but instead has the audience rooting for him the entire way, whether it’s wanting him to defeat Apollo Creed, or wanting to see Rocky finally win over Adrian. Sylvester Stallone’s performance as Rocky Balboa is pitch perfect – the writer-star clearly knows his strengths as an actor, and plays them up. Stallone’s Rocky is kind-hearted and maybe not the sharpest tool in the shed, but his goofy charm wins over nearly everybody he encounters in his day to day life. Everybody in the film is seemingly a fan of Rocky’s – he’s just one of those inherently likable kind of guys. Talia Shire’s turn as the timid and quiet Adrian is wonderful as well, with the actress only coming out of her proverbial shell when she begins to see Rocky romantically – and even then, she constantly seems like a nervous wreck. Shire and Stallone have great chemistry together – their first dates together feel like genuine first dates, and most of their initial interactions are believably awkward. Supporting performances from both Burt Young as the angry and bitter Paulie, and Burgess Meredith’s grizzled veteran trainer Mickey are both incredible, and saw both actors nominated for Best Supporting Actor. The loud and rowdy pair of Paulie and Mickey serve as great contrasting figures to Rocky’s quiet, often stoic personality. On top of some terrific performances from the entire cast, Bill Conti’s uplifting score sets the tone for the inspirational and personal story to come. Conti’s “Gonna Fly Now” and “Going the Distance” are two of the best movie compositions ever performed, and help give some dramatic weight to the film’s final act. When “Going the Distance” reaches its final moments and Adrian makes her way through the crowd to greet Rocky, you know you’ve just experienced something truly magical. Rocky is, in my opinion, one of the most satisfying movie going experiences you could ever possibly imagine – it has drama, humor, an amazing and relatable love story, a great score, incredible performances, and one of the most iconic underdogs in movie history. Rocky is a Hollywood masterpiece, and is the kind of movie that seems all too rare today.

Billy Wilder’s Best Picture winning The Apartment is the cynical old master of cinema at his most heartwarming and endearing. The film starring the charming Jack Lemmon in quite possibly his most enduring role and a young, hilarious Shirley MacLaine was one of the very first “classic” movies I ever saw, and one that immediately won my heart. The Apartment tells the story of C.C. Baxter (Jack Lemmon) a down-on-his-luck pushover who rents his apartment to his many bosses so that they can carry out affairs with younger women. Baxter does so in order to climb the often difficult to navigate corporate ladder, and his strategy pays off in spades. After falling in love with the workplace elevator girl Fran (Shirley MacLaine), Baxter begins to have a change of heart. When he finds out that Fran had previously been seduced by his boss Sheldrake (Fred MacMurray) and the two had carried out an affair, things become complicated for the love triangle. The Apartment is Billy Wilder and I.A.L. Diamond’s strongest writing work together, in my opinion. The story features much of Wilder’s inherent cynicism, mostly in C.C. Baxter’s view of the world, and in Fran’s dealings with Sheldrake – there’s a lot of hopelessness and bitterness to be found. Luckily, both Wilder and Diamond also show a deeply human side to their writing, something they would continue to improve on in future scripts. It seems that Diamond brought out the very best in Wilder, making him look past the negatives and create something with spirit and heart. The love story the two men have crafted in The Apartment is truly touching and multi-layered, making it easily one of the most effective romantic-comedies ever made in Hollywood. C.C. Baxter is one of my all-time favorite screen characters – there’s something I find so compelling about his depressive and cynical, but deeply romantic and well-natured attitude. Jack Lemmon’s performance as Baxter is incredible, picking up a well-deserved Best Actor nomination at that year’s Academy Awards. Shirley MacLaine’s turn as Fran is equally as complex, with the sweet young woman towing the line between naive and entirely self-aware. The blossoming romance between both Baxter and Fran is entirely believable, and incredibly sweet – there’s something in the air when the two characters interact, especially in the latter half of the film when they share more screen time. Fred MacMurray’s supporting role as Sheldrake is probably the most I’ve ever enjoyed seeing the actor on screen – he is perfectly charming and unlikable when contrasted with Jack Lemmon’s endearing C.C. Baxter. MacMurray was always best used as a supporting player, and Wilder once again uses him to great effect in The Apartment. The film would go on to win Best Picture, Best Director (Wilder), and Best Writing (I.A.L. Diamond and Wilder) at the 1961 Academy Awards, creating the structure and style of modern romantic comedy films, and paving the way for generations of rom-coms to come. The Apartment is sweet, intelligent, funny, and deeply moving in a way that Billy Wilder was never quite able to recapture – though his 1961 film One, Two, Three is a personal favorite of mine.

The Godfather has been parodied and paid tribute to time and time again, in various mediums and to varying degrees of success – its immediate influence on popular culture and media in general is undeniable. Francis Ford Coppola’s Best Picture-winning film follows crime syndicate Don Vito Corleone (Marlon Brando) and his children Michael (Al Pacino), Sonny (James Caan), Fredo (John Cazale), and Connie (Talia Shire), detailing their relationships with the syndicate, with each other, and the power held by the Corleone family and its individual members. After Vito is shot in an assassination attempt and subsequently hospitalized, his sons Michael and Sonny do what they must to maintain power in the dark and dirty world of organized crime. Coppola’s The Godfather helped to once again popularize the gangster drama, as it had fallen on hard times after the 1940’s. It did this by featuring some of the most iconic characters to ever be featured in a Hollywood film, most notably Marlon Brando’s incredible take on Vito Corleone, the wise, calm and collected Don and patriarch of the Corleone family. Al Pacino’s Michael Corleone is also introduced in the film, starting out as a kind-hearted and ambitious young man and quickly climbing the ranks of the syndicate after the hospitalization of his father. Pacino’s Michael would go on to be further developed in Coppola’s later two films in the Godfather trilogy, turning him into the complex anti-hero we would eventually know him to be. Also noteworthy is Robert Duvall’s Tom Hagen, the right-hand man or consigliere of Vito – his quiet, sensible nature makes him stand out from the pack. The Godfather features incredible cinematography from Gordon Willis, who plays a great deal with light, creating a dark, murky, natural atmosphere that makes The Godfather feel genuine. Nino Rota’s musical score also helps to set the tone of the film, using many stereotypically Italian compositions and a heck of a main theme to set the scene. Francis Ford Coppola’s up close and personal look at the Italian mob changed films forever, and would inspire many subsequent crime films with dark, violent, and natural tones – an effect we’re still feeling today. My favorite moment of the film comes in the form of a violent montage at the end of the film – it showed a younger me just how powerful and exhilarating classic cinema can be. Though The Godfather clocks in at nearly three hours in length, its tight pacing, incredible script, and powerhouse performances makes the time absolutely fly by – by the time it’s over, you’re thanking yourself that you still have two more films in the series. The Godfather is a must-see for anybody interested in film, and is endlessly entertaining and influential.

Casablanca is another film on my list that has been talked about by fans, critics, and historians for decades, and one which few revelations can still be made about. In my opinion, it’s one of the most perfectly constructed films ever made, featuring a tremendous romantic plot, humor, action, style, and suspense – what else could you ever need? Casablanca takes place in the titular city of Casablanca, Morocco during World War II, where people of many political and social allegiances come to enjoy the sights and nightlife. Rick Blaine (Humphrey Bogart) is a proprietor Casablanca, running “Rick’s Café Américain” where he has made a name for himself, and formed relationships with people of all cultures and beliefs. Rick soon meets a former lover named Ilsa Lund (Ingrid Bergman) and her husband Victor Laszlo (Paul Henreid), who bring with them a number of complications that Rick thought he had finally escaped. Casablanca is a film that is better viewed with little knowledge of the major plot points, as it has been parodied and paid homage to on dozens of occasions over the years. It’s screenplay is one of the greatest in the history of film, using quick, snappy dialogue to push forward the already fast-paced plot. The chemistry between all of the main characters is incredible, especially between those who are more permanent residents of Casablanca – Bogart’s Rick is familiar with every face that walks into his cafe, and has a different rapport with each of them. When Bergman’s Ilsa finally comes into play, it’s immediately apparent that Rick holds some resentment towards her, taking it out on his piano-playing friend Sam (Dooley Wilson) – who manages to always take it in stride. Bogart and Bergman are electric together on screen, making their scripted romance feel genuine and lifelike. Both legendary actors put in some of the best works of their impressive careers, thanks in part to the Academy Award winning screenplay by Julius J. and Philip G. Epstein, and Howard Koch. The way the screenplay uses humor and suspense concurrently feels incredibly modern and refreshing, making Casablanca feel like it hasn’t aged a single day. Director Michael Curtiz’s vision of the city of Casablanca is dreamy and idyllic, especially for what was such a complicated and turbulent time for most of the world – it’s a place anybody would want to travel to for a few days, if only to get away from the complications of everyday life. The characters are all fully realized and endearing for their unique character traits, with Rick, Ilsa, Sam, Victor, and Captain Renault (Claude Rains) being some of the all-time most memorable in classic films. Casablanca is a masterpiece from start to finish, and a perfect example of how a screenplay can almost single-handedly carry a film. Luckily, great performances and inspired direction push Casablanca over the edge, creating one of the all-time greats.

My first experience with George Roy Hill’s zany The Sting came just this past year on the big screen – when the credits rolled and walked out of the theater, I was giddy and wholly satisfied. The Paul Newman – Robert Redford starring film hit all the right marks dramatically and comedically, drawing the audience in with a compelling script and some terrific performances. When the film’s unexpected ending finally arrived, I was absolutely floored – The Sting, a film about deception, had swindled its viewer. The Best Picture winning film sees young con artist Johnny Hooker (Robert Redford) getting in way over his head and ripping off the wrong people. His unintentional actions anger kingpin Doyle Lonnegan (Robert Shaw), who seeks to have the mysterious young con artist killed at any expense. Hooker decides to seek refuge with famed con-man Henry Gondorff (Paul Newman), and the two men devise an elaborate plan to pull off the ultimate con on Chicago’s most dangerous man, Doyle Lonnegan. The film was nominated for ten Academy Awards in 1974, picking up statues for Best Picture, Best Director (George Roy Hill), Best Original Screenplay (David S. Ward), and Best Music (Marvin Hamlisch). David S. Ward’s screenplay for the film is brilliant in every way, using scenes of action and suspense constantly keeping viewers guessing, and employing comedic scenes to further the relationships between the cast of characters. Each of our three main characters are believable and fully realized, all of whom have their own motives and reasons for being involved in the dangerous world of conning. Ward’s build-up of The Sting’s long con is perfect in its pacing – even leading viewers on the wrong path on some instances. Director George Roy Hill matches the pacing of the screenplay with an often frantic pace, setting many scenes to the music of ragtime pianist Scott Joplin – most famously his endearing “The Entertainer”. Even with a great script and some highly energetic direction, The Sting would be nothing without the terrific chemistry between actors Robert Redford and Paul Newman. The two legendary actors play off each other in a way that few cinematic pairings can match, resulting in more than a few memorable dramatic and comedic moments. The performance of Robert Shaw as the villainous Doyle Lonnegan is my personal favorite aspect of The Sting – he steals the show with a scenery chewing, occasionally over-the-top performance, but Lonnegan never feels like a joke. Despite seeming larger than life in almost every way, Shaw’s Doyle Lonnegan still manages to be menacing and threatening. The Sting is an incredibly well-written and acted film, resulting in the most fun I had in a theater in 2016.

William Wyler’s biblical epic Ben-Hur is the movie that served as my introduction to classic films, creating a lifelong obsession with the silver screen in the process. I saw it as part of my grade 7 religion class all the way back in 2003-2004, and was captivated by every minute of the 3 ½ hour film. Ben-Hur tells the classic story of Judah Ben-Hur (Charlton Heston), a wealthy prince living in Jerusalem with his mother (Martha Scott) and sister (Cathy O’Donnell). His best friend is a man named Messala (Stephen Boyd), who after some time away from Jerusalem, returns to the city as a commander of the Roman garrison. After an accident nearly costs the life of the governor of Judea, Ben-Hur is sent to the galleys by his once best friend, and his family imprisoned. What follows is an adventure the scale of which had rarely been seen on screen before 1959. The film spans several years, and sees the rise and subsequent fall of Jesus Christ, who plays a prominent figure in the film. Wyler’s Ben-Hur is mostly remembered by the public for its incredible chariot race scene, which is still just as thrilling and visceral today as it was more than fifty years ago. The film’s few action scenes feature a sense of realism and brutality that is not often seen in film’s of this era, and adds to Ben-Hur’s unique nature. It’s never exploitative in this way, but instead uses its visceral nature to further the story along, and convey the weight of the situations faced by Judah Ben-Hur and those around him. Charlton Heston’s performance as the titular character is tremendous, bringing an undeniable charm and charisma to the role that has proven to be unmatched in subsequent retellings of the story. While Ben-Hur is more than 3 ½ hours long, it never feels slow or bogged down by its run-time, mainly due to its incredible writing and pacing. Every scene feels meticulously crafted and has a sense of purpose, and major milestone moments are evenly spaced out throughout the film. An example of the film’s excellent sense of pacing comes in its final act – even after the chariot race is done, the film manages to keep its hold on viewers with a rigorous journey to the leper colony, where we finally get some much needed emotional payoff. Ben-Hur would go on to win 11 Academy Awards in 1960, including Best Picture, Best Director (William Wyler), Best Actor (Charlton Heston), Best Supporting Actor (Hugh Griffith), and Best Cinematography – only losing in one category. Every minute of Ben-Hur is captivating and finely crafted – there’s no wonder why it was so well-received by a 12-year old me.